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The Wandering Sapphire	By : justheretoread Category: -Misc TV Shows > Threesomes/Moresomes Views: 3863 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not own Critical Role and I do not make any money off of this work.

Chapter List
- 1-The Del Rolos
- 2-Chapter 2, Allura and Kima
- 1
- 2
Jester, Beau, and Yasha walked through the Cloudtop district of Emon. “So Jess, do you know where we are going? We’ve been walking for an hour around for an hour. I think we’re starting to get looks.”
“It’s called the Ivory Tower, Beau. How hard can it be to find? I’m sure we’ll see it.” Jester pointed at the city around them. “Besides, look at the houses. It’s so different than Nicodranas.”
As they walked, Yasha and Beau noticed someone following them. As Yasha’s hand went to her sword the guard spoke up. “Excuse me, miss, are you three looking for something?”
The guards with him all eyed Yasha. Jester looked around. “O, yes. Do you know where the Ivory Tower is?”
“I do. What is your business there?” While the guards calmed down as Yasha let go of the sword, they were still on edge.
Beau spoke before Jester could. “Arcanist Allura Vysorsen has requested her service, for a, um, personal matter.” She pointed at Jester, the most well dressed among them in her usual green cloak.
“And you two?” Beauregard was wearing a jacket over her usual clothes and Yasha was in her usually hides. Neither looked at home in the richer area of town.
“They’re my friends.” Jester said quickly. “And my bodyguards.”
Satisfied with the explanation, the guard directed them to the Ivory Tower. Beau spoke up. “I told you we’ll stand out.”
Jester just chuckled. “Yes, well we always do. But come on, I need you two here. While mama doesn’t think anything bad is going to happen, she never met these clients before. And I’m going be tied up. And gagged.”
Yasha blushed at that. “Jester, if you don’t feel safe” she began before being cut off.
“I feel plenty safe. Any red flags and I don’t accept the job. I made that promise to mama. But you never know. There’s a reason mama keeps Bluud nearby. Plus, getting lost in a moment of passion can be just as dangerous as anything. You and Beau just need to run in if you hear me safeword or something. I should be able to move my mouth enough to cast thaumaturgy. Between you guys and The Traveler always watching, I’ll be fine. Ooh, is that a bakery? We got to try that on the way back.”
The trio walked up to the white tower and knocked on the door. A few moments passed before a tall human woman with blond hair and a blue dress answered. “Hello, you must be The Wandering Sapphire. I am Arcanist Allura Vysorsen, of the Tal’Dorei Council, please come in.”
Yasha and Beau straightened up as they followed Jester. “Please to meet you. I’m Jester, and these are my guards, Beauregard and Yasha.” Allura guided them into the room.
A halfling with darker blonde hair, tan skin, and a scar over her eye greeted them. “3 of them, Allie? I know we wanted to experiment but…”
Jester saw that Kima was a bit nervous. “You must be Lady Kima. I’m Jester, the Wandering Sapphire. Don’t worry, these are just my bodyguards, Beau and Yasha.” Kima saw Yasha’s sword and calmed down.
“Ah, I guess that makes sense. You two see a lot of action?”
Yasha blushed. “Well, um, this is the first time Jester asked us to um supervise a client but it’s not like we’ve never”
Beau nearly face palmed. “I think she meant with my fist. Or your sword at least. We came across a few bandits right after Whitestone but nothing much.”
Kima nodded and began talking with the two guards about the fight. Allura frowned and pulled Jester aside. “Supervise? I wasn’t expecting to be watched”
“O, don’t worry. They don’t need to be in the same room, just right outside the door. Or I have a few curtains in my bag we can use if there isn’t a door.” She patted the pink haversack. “I do not mean to offend, Lady Allura, but your wife and yours request will put me in a vulnerable position. And you two came without any recommendation from mam, I mean Marion, the Ruby of the Sea or any of the local guilds around her.”
“Well I guess that makes sense. We haven’t really done anything like this before but we thought it would be fun. But Kima and I both agreed we both needed to be in charge of the situation to avoid any thought of jealously and stuff.”
Jester had the biggest grin on her face. “That’s real sweet and makes perfect sense. Communication and knowing both your partner’s boundaries and your own is key. Don’t worry, Beau and Yasha are just here in case things get out of hand. You won’t be the first clients who didn’t notice a safe word or a hand signal because the scene was too damn sexy. I mean, you’re going have me all tied up and gagged while you two have your way with me. And I look forward to it. But just in case my cute little body distracts you from noticing something, I need Beau and Yasha nearby to communicate to. I should be able cast thaumaturgy” at that a window across the room opens “with a gag in. As long as you don’t tie me up with anti magic cuffs.”
Beau and Yasha heard that and looked over. The three shared a somber look. “So, how exactly do we do this?” Kima asked. She sensed the silent conversation between the three was best left silent.
Jester perked back up at that. “O, well first there is the payment we’ve already talked about. Then we’ll go over safe words and what is expected and everything. I assume we’re going to another room?”
“Ah yes.” Allura passed a large purse filled with gems and gold to the tiefling.
Beau spoke up as Jester counted. “This bag isn’t magic, is it? Not a bag of holding or anything like that?”
Kima frowned at that.“No, it’s just a bag, why? The messages back and forth didn’t say anything about magic.”
“It’s just to avoid opening a rift in the dimension, dear. I told you a thousand times never to put a bag of holding inside a bag of holding.” Allura put a hand on her wife’s shoulder.
“Wait, that’s actually a thing? I just thought you and Drake didn’t want to end up with 8 bags inside of each other and forgetting which one had the thunder potion or whatever.” Her wife laughed at that.
Jester finished counting and took out most of the gems. She placed them in a special pocket of the haversack. The rest of the payment went into a different pocket. Allura heard a small poof. “That isn’t just a pocket dimension in there, is there? That sounds like a small teleportation circle.”
“It’s so cool. Widogast’s Teleportation Pocket. A friend of mine made it before we parted ways in Nicodranas. Can only teleport nonorganic matter or something. Just in case a bandit gets lucky.”
“That sounds interesting. How exactly did they get the spell to work inside a pocket plane like the haversack, that would cause the same feedback loop…”
Kima tugged on her wife’s arm. “Allie, you’re talking shop.”
“Right, sorry. Follow us upstairs. Carefully, you can get a bit lost.” The three followed. Allura conjured some chairs for Beau and Yasha as she led Jester into the room.
Jester looked back at her friends real quick. “Just remember, if you hear Hupperdook or the door slams open rush in.”
Yasha just nodded and blushed. “You can trust us” Beau confirmed.
“I know.” Jester looked around the room. “Well, this is unexpected.”
Kima rolled her eyes “And what exactly did you expect? A bigger bed with gold entrusted tapestry everywhere and pillows worth their weight in platinum?” She was used to other council members flaunting their wealth.
“Actually, I was expecting it to be more of a sex dungeon. A hitching post somewhere, some manacles showing, and those toys your request mentioned displayed all over. This is clearly not your bedroom.” Kima raised an eyebrow. “That bed wasn’t slept in for at least a week and there is nothing really personal here. Plus the path to get here was too long for regular use. I mean, I understand. A lot of people keep a separate room for the less orthodox pleasures.”
Allura fiddled with a chest at the front of the bed. “You know, that wouldn’t be a bad idea. I bet Kima would love that. But this is just a guest room. However, this chest is connected to a few others” Allura muttered a quick spell and began pulling this out.
Kima laughed. At her wife and Jester’s looks she explained. “Sorry, I was just picturing Highbearer Vord walking into a sex dungeon instead of his guest room in the middle of the night. I bet he’ll look for other places to stay whenever he’s in town then.” Jester giggled at that. She knew The Traveler would have approved. “So, do we just begin?”
“Actually, if you don’t mind I would like to inspect the instruments you want to use.” Her tone made it clear that this wasn’t a request.
“Of course.” Allura was already digging out a selection items. “Honey, which ones did you want to use?” Kima gave her a looked as if they went over this before. “What, it’s your collection. I barely know their names.”
Kima walked over to help her wife. “You like using them on me well enough.” She bent down and kissed Allura’s cheek before digging through. “Let’s see, where are you? Mm, this can be a warm up.”
Jester looked at the thick green dildo came up and grinned. “Ooh, is that a half-orc? That knot is so detailed. I can never find one that does it justice.”
“Yes, it’s named Matuk. And it pulses and twitches as if it’s real.” Jester gasps as it wriggles in her hand. “It can even cum. Requires a magic word so never too early, better than the real thing.”
Jester fondled the toy in her hand. “I don’t know about that, but whoever made it should be proud. My supplier can just get them to vibrate and considers that a feat. When I asked for a knot she just gave me one that widened at the base. I swear, that old lady never saw an orc naked.”
“Gilmore has plenty of hands on research there. You should check his shop out, Gilmore’s Glorious Goods. Just say I sent you, and that you’re looking for the sex stuff. Otherwise he’ll try to sell you an axe or something.” Kima pulled out another toy. “Mm, this is a possibility.” She throws up a red cock that almost came to a pointed tip.
“O, tiefling. Nice.” She grabbed it. “And it’s heated. Nice touch. Kinda big though, I take it your wife enjoys that?”
Allura measured out some rope as she sighed. “Not particularly. Kima’s the ‘size queen’ as she so eloquently says it. She’s surprisingly, um, flexible I guess.”
“Yup. I like them big. And artificial.” The giant platinum colored, scaled dildo she pulled out next emphasized Kima’s point.
“Mm, that’s isn’t a dragonborn, is it? But it’s beautiful. What’s it’s name.”
Allura rolled eyes. “She calls it Bahamut.” Kima playfully punched her. “What, you do. Now I wonder what the Highbearer will say about that form of worship.”
Kima raises an eyebrow. “Well you can always ask him next time we’re at a stuffy dinner. It’ll liven the room.”
“O, you worship Bahamut? I always thought his followers were a bit stuffy. If I knew you could be this fun I wouldn’t have drawn dicks all over… Hey, have you ever heard of The Traveler? He’s my god, but not very people know of him. He visited me in my bedroom when I was a lonely kid and always been there for me.”
“Your god visited you? When you were a kid? In your bedroom? Um, are you sure he was a god?” Allura asked hastily. She had heard some rumblings of a new cult, but nothing to give her too much concern.
“Well, if he wasn’t a god could I do this?” A bunch of sparkly pink hamsters with unicorn horns swarmed around the tiefling.
“Certainly looks divine to me.” Kima poked one of the hamster-unicorns. “So, do the toys meet your approval?”
“O yes. Mm, And that rope seems perfect to tie me up tight without cutting off the circulation. But the message from the Lavish Chateau mentioned a gag? Can I see how it fits and feels first, gags can be tricky.”
Kima tosses a small belt at her. “Here, knock yourself out.” Jester fiddled with it a bit. Like the rest of the couple’s toys, it was finely crafted. She examined the small ball that was clearly going in her mouth. It seemed normal enough, although the ball flattened out on the other side.
“Is something supposed to go here? And these markings look magical.”
Allura saw a tiny bit of concern on the tiefling’s face. “Ah yes, that has the same enchantment as my harness.” She showed the leather belt and grabbed the half-orc dildo. She placed the base to the middle and the slot expanded a bit and the cock was attached. “Although this one also has a sensory enchantment on it so the wearer can feel it as if it was their own flesh.”
Jester’s eyes lit up. “I certainly need to visit Gilmore’s. That can make things a lot more interesting. I bet even The Ruby of the Sea would want one.” She finished inspecting the gag.
“Now we need to go over safe words, limits, and etiquette. As I’m the one being tied up, this will mostly be about me but also both of you may get uncomfortable during this. If you do, there is no shame in letting us know so we can either take things slow or stop altogether. My safe word is Hupperdook. If I say it or if you think I say it (although really, Hupperdook is such a specific word it is hard to mistake, which is part of why I picked it). The requests you sent doesn’t seem to be anything close to a hard limit, although is there anything you didn’t mention in this list you may be interested in?” She point to a large piece of parchment and looked it over. “I see here you don’t mention anything about impact play, spanking, or choking? It’s totally find if that isn’t you thing, it’s just something I would prefer to not be surprised by and often comes along with bondage.” Jester rushes as she spoke to get the entire thing out before Allura could answer with a barrage of questions. She found she usually covered most of them if she could just get through the speech. “Also, feel free to mention anything you like, don’t like, or flat out refuse although Lady Allura seems to have been thorough”. She again looked at the message.
Kima came up to read over her shoulder. “Wow, how many sendings did it take to send that? Mm, toys, rope, fisting, anal, oh really Allie, you said ‘sharing of the professional’s oral facility as she provides the customers with physical pleasure’?” She kissed Allura quickly. “You’re adorable. Mm, she seems to cover all the basics. Although that minx will probably go after those tasty looking tits of yours too. She’s a bit of a biter with those, but not enough to leave a mark.”
Allura blushed. “Well, they do look lovely. Also, um, me and Kima aren’t sure how we’ll react to kissing someone else or seeing our wife doing it. It may seem a bit trivia with what we are about to do but”
Jester cut her off. “I understand. Different acts have different levels of intimacy for everyone. I’ve had one couple where someone just watched and felt that if they had sex with me it’ll be a betrayal as I banged the hell out of their partner. Others kiss me on the mouth the second we’re in a room together. Trust me, this is supposed to be enjoyable so whatever you’re okay with. Now, are we ready to start?” Jester took off her cloak in preparation.
“Almost, I just need to get 1 thing out.” Allura cast a spell and a small black padded table with a few cuffs on them appeared.
Kima was still reading the written down requests. “Hey, why is there some added writing to this? Looks like scribbles.”
“O, yea, ‘light humiliation-emphasis on naughty name calling.’ Calling me a ‘dirty little slut’ and stuff like that. Your wife called it ‘humiliation’ but I had to get her to be more specific. The stuff people want to call me or be called can get pretty out there. I once had a guy call me an evil demon spawn, and that just got awkward without any fun roleplay talked about beforehand.” Jester realized she was babbling by the look on their faces. Kima was lost and Allura looked ready to write an essay on the subject. “Anyways, how do you want to begin?”
“Strip”. The blue professional obeyed Allura. As she did, Lady Allura approached and took the clothes. She folded them and put them off to the side of the room.
Jester smiled. “Thank you.”
“On your knees, slut.” Kima was already naked on top of the table. Her legs were already spread and waiting.
“Go on, pleasure my wife. I’ll join in a minute.” Jester crawled over to the table. The tiefling moved quickly between the bronze halfling’s legs.
“So, do you want me to tease you slowly on the edge or” before Jester could finish her question Kima grabbed her horn and guided the blue head between her crotch. Allura giggled at her wife’s impatience. Jester took the hint and began licking.
“Lady Kima, where are your manners?” The wizard kissed her wife.
“When did I have manners?” She moaned as Jester picked up the pace. “Fuck, she’s good Allie. I mean, she isn’t you but, fuck”.
Allura glided reached down and glided her finger along one of Jester’s horns. “Well that is what we hired her for. A little slut for both of us to enjoy.” She took a firm grip of the horn and gently tugged. Jester quickly moved between the human’s legs. “Right there, that’s it.”
The Wandering Sapphire kept eating whichever cunt was in front of her as the wives passed her back and forth. Soon Kima laid on the table moaning with Jester’s blue head between her legs and Allura switching between the halfling’s breasts. “Fuck, come on Allie, just a little more. Please, let me cum all over this slut’s face. That blue adorable face of hers will look so hot covered in my juices.”
Allura lingered on Kima’s nipple as she savored the look of pure need on her wife’s face. “You heard her. Go on, Jester, make my wife cum.” At those words Jester sped up. Kima was already close. Allura moved down and shoved the traveling concubine’s head even deeper in. Kima moaned as she finally came. Allura whispered into Jester’s ear. “She tastes great, doesn’t she?”
“Tasty” she said from between Kima’s legs. The halfling rode out her orgasm with the tiefling’s help. Slowly Kima came down off her high. She looked down and saw the blue face covered in her juices. “How do I look?”
“Fucking hot.”
“She’s right.” Allura bent down to lick Jester’s face. “Mm, delicious. Now get up, sweetie. That’s where Jester’s going.” Kima got up quickly and sat on the guest bed.
“Take your time prepping her for your big plan, Allie. Enjoy this, no need to rush to the end.”
Allura walked over to the table and started fiddling with the different straps and cuffs. “I will, Kima. Besides, looks like you can use the break.” Kima rolled her eyes but watched eagerly. “Now come here, Jester. Lie down.” She cuffed Jester’s hands down to the sides of the table near her head. “Is that too tight?”
“Nope. Perfect” Her arms jiggled for emphasis. “Oooh.” She was surprised at the sudden attention to her breasts. Allura just smiled around one of Jerster’s dark blue nipples. “Thanks for the warning, Lady Kima.”
Kima chuckled a bit from the bed. “Brace yourself. My wife can spend hours worshipping a gorgeous pair of breasts.”
“You won’t hear me complaining. She certainly knows what she’s doing.”
Allura continued sucking on the hardened nipple before switching to the other. She licked, sucked, and playfully nibbled on the full breasts in front of her. Her tongue glided all over the blue mounds. It dipped between the two before climbing up again, the wizard memorizing every inch of those tits. Jester just moaned at the attention, unable to grab the council member’s head to make sure that mouth lingers just a little bit longer before moving on to the other breast.
Kima watched for as long as she could. “Aww, darling, I think the slut wants a little more. Hear that, she’s practically whining like a puppy now.” Before Jester could retort she felt the gag on her lips. “Open wide, slut. There, that’s a good whore.” Kima tightened the gag around Jester’s head. “There, is that good?” Jester nodded.
“Imm goooooooooo” Jester muffled out from behind the gag.
Allura finally took her mouth off of the blue tits. “Perfect, that should be enough for her to cast a cantrip. Now, Kima, do you want to add the attachment already? I could work around that.”
“Nah. I think I’ll still watch for now. My cunt is going be sloppy after watching you fuck this slut and stretch her out.” Kima returned to the bed. “Besides, I know you love watching me fuck myself, Allie. Just give me reason to.”
Allura moved down the table and grabbed Jester’s leg. “Here, spread it just like this. I want access to both holes.” She grabbed the rope and tied Jester’s legs to the table. She took a step back to just look at Jester gagged and tied to the table with her legs spread open. “Beautiful. And look, Kima, she came already plugged.”
“Smart girl. Bahamut knows you’re going do your best to open that hole up. I had to grab extra lube just out of fear of what you’ll do with another ass to fuck.” Allura rolled her eyes at the ribbing.
“Sure, make me out to be the one obsessed with tits and ass. As if you don’t have your own kinks.”
Kima gave a mock horrified look. “Me? Kinky? Why, you would think I just paid an absurd amount of money just to tie up some helpless girl alongside my wife.” Her look broke with a laugh. “Come on Allie, I love how much you appreciate the female figure.”
The wizard shook her head. “You also love giving me a hard time about it.” She blew her wife a kiss. “But then, that is why I fell for you.” She turned her attention back to Jester. “What do you think, honey? Should I leave it in and go slow, warm her up?”
“Take it out and fuck that ass.” Kima’s fingers were now between her own thighs. “She’s slopping wet already. Use Beezle for it though, Matuk will destroy that fuck hole way too soon. Plus you can use it later.” Allura took her time putting the harness on. She grabbed the big, red cock with bumps around it and held it to the harness. The material shimmered pink as the dildo attached itself.
Allura then grabbed the small green ring at the end of Jester’s butt plug. “Mm, nice and easy.” She slowly began to pull plug out before pushing it back in. She fucked Jester for a few minutes with the plug before removing it with a final twist. “There, opened up just enough for some fun.” The wizard spread some lube around her fake cock before placing at Jester’s asshole. She nearly whispered “are you okay?”
Jester eagerly nodded. Louder, Allura spoke “Your slutty little whore ass is going enjoy this, slut.” She was slow but steady, thrusting the cock into the tight hole a few inches at the time. Allura grunted as the dildo’s magic worked. “Fuck, your hole feels so good.”
Eventually Kima got too excited to keep to herself. She was holding the giant platinum colored dildo. “That looks so good Allie. You’re fucking that slut ass. Do you mind stopping so I can use her mouth?”
“Of course, honey. Besides, seemed to enjoy the knot so much I think we should give her a test drive.” Jester tried to see what was going on but it was too much. She saw Kima approach her and held the base of the large, scaled dildo to the bald gag. Up close, Jester would have thought it was actually the size of a dragon’s cock. It attached to the flat side of the ball gag at the same Allie attached the second cock to her harness.
“Mm, she looks more than ready.” Jester looked back at Allie. The large, knotted orc cock was position on the same harness as the one that been plowing her ass.
Jester couldn’t help but muffled out “fuck me” at the sight.
“Hear that, Allie. I think we found the perfect whore for you. She wants you to fuck both her holes while she watches me fuck myself on this giant dragon cock.” Kima stood over Jester’s head, positioning her cunt right over the dildo. She waited for her wife to get into position.
Together, the two women moved. Jester’s ass and pussy were filled at the same time Kima lowered herself down. The two women wasted no time. They were both too eager to fuck the blue tiefling tied up beneath them to take it slow.
Jester moaned around the gag as Allura fucked both her holes. She savored the unique feeling of two cocks being thrust into her by a single person. Her ass was once again filled with that long, hot tiefling cock while her pussy was knotted. She was used to both feelings separately, and even been double stuffed enough times to know how that felt but this was different. With a single thrust each hole was filled, and only one person had to pull back for Jester to feel empty.
All the while, she watched the small form of a halfling slam herself down onto the cock coming out of her mouth. “O Allie, this is so good. Fuck, Bahamut, so big. Fuck.” Jester thought the halfling was splitting herself in half for that pleasure. And she couldn’t blame her. The two cocks inside of her were bigger than most of her clients and Jester wanted more.
Allura went faster and faster, too focus to even curse. The harness meant that she felt both of Jester’s holes as they fucked. She reached forward and grabbed Kima’s tits from behind. “Fuck, Allie, that’s it, fuck this whore while I fuck myself all over her face. Fuck, Allie, I love you so much. Fuck!” At that moment Allura kissed Kima’s neck as she kept fondling her tits. All three women came within seconds of each other, Jester unable to anything but take it.
The tiefling couldn’t even smile as she watched the wives make out over her body as they drove each other on to another orgasm.
As Kima and Allura came down from their pleasure soon the wizard panicked. “O no, o no, Hupperdook, Hupperdook, damn it, help someone.” Kima looked at where Allura was pointed at and Jester’s body. Before she could explain to what happened, Yasha and Beau were in the room.
“What’s wrong, what happened?” The two body guards were on high alert.
“I don’t know, all was going fine but I guess I must have been going too hard and not notice a sign or something and she passed out, I think I saw her eyes roll back. She could be having a stroke or something. Kima, get that gag off her, check if she’s breathing.”
Beau burst into laughter. Kima quickly joined her as well as Yasha bent down to check. “What’s so funny? I mean, I didn’t mean to hurt her or anything.” Yasha took the gag off Jester and gentle caressed her cheek. She had experience with this.
“Hey, Jess? Hey. Good time, huh?” Jester opened her eyes and saw the panicked look in Allura’s face.
“O fuck. I haven’t been fucked that well by a client in months.” She looked around at the rest of the room. “Um, Beau, Yasha, why are you here?”
Kima answered that question. “Sorry, my wife is not the most experienced when it comes to sexual partners. I think you’re the first woman who passed out on her. I got a bit more stamina than most. Although I’m a bit of a squirter. Allie just thought you were in danger and called in your friends. Either that or she wanted to show off our toys.” She looks over at her wife once again. “It’s fine, Allie. You banged her so good she fainted. It happens sometimes, especially after multiple orgasms.”
Allie began to blush. “Oh, that makes sense. The process of an orgasm can take a lot out of the body, especially multiple ones in such a short time. Um, sorry for”
Jester interrupted her. “Nothing to apologize for. You thought there was a problem and you got help. Thank you. Besides, I haven’t had a client make me pass out in months. Trust me, this was my pleasure.” She was sipping on some water that Beau passed her.
As the body guards left the room Beau gave a confused Allura a high five. “Good job, trust me that isn’t an easy feat”.
The Wandering Sapphire and her companions made small talk as they cleaned up and got dressed. Jester asked some questions about Gilmore’s shop and the city as she tried to ease Allura’s embarrassment. As she left she gave them a small business card to contact her again.
Jester, Beau and Yasha soon departed the tower. It was still late afternoon. “So where to now, Jester? Want to just rest up at the inn? We can take care of your tithe tomorrow.”
Jester just smiled. “Nope. Let’s go get Molly, then we’re going shopping. Kima told me of this awesome store.”
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The Wandering Sapphire